Beta-Propiolactone → HCID 14051190, compound

HRID 1199711Notes

Reaction equation

HRID 1199711 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:5]=[C:6]([CH:18]=[CH:19][CH:20]=1)/[CH:7]=[CH:8]/[C:9]1[S:10][C:11]2[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=2[N:13]=1.[C:21]1(=[O:25])[O:24][CH2:23][CH2:22]1>CN(C)C=O>[C:21]([CH2:22][CH2:23][O:3][C:4]1[CH:5]=[C:6]([CH:18]=[CH:19][CH:20]=1)/[CH:7]=[CH:8]/[C:9]1[S:10][C:11]2[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=2[N:13]=1)([OH:25])=[O:24]

Participants

5

Reactant 3

HCID 2365Beta-PropiolactoneHCID 24758Sodium hydrideHCID 7986269HCID 7986269, compound

Product 1

HCID 14051190HCID 14051190, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 3 ml of dimethylformamide were added 47 mg of 60% sodium hydride and 300 mg of 2-(trans-3-hydroxystyryl)benzothiazole, and the mixture was stirred at room temperature for 30 minutes. Then, 74 μl of β-propiolactone was added and the mixture was further stirred for 4.5 hours. The acidic portion was extracted in a conventional manner with chloroform, and after drying over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure and the crude crystals were washed with ethyl ether, followed by drying under reduced pressure to give 118 mg (yield 31%) of the title compound.

Workup

  1. stirringthe mixture was further stirred for 4.5 hours
  2. extractionThe acidic portion was extracted in a conventional manner with chloroform
  3. dry with materialafter drying over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. washthe crude crystals were washed with ethyl ether
  6. customby drying under reduced pressure

Sources & evidence

ORD record
ord-3bd1d03938264996b127f88aab870173
Source dataset
uspto-grants-1990_02
Patent number
US04902700

Reaction notes

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